Acetic Acid → HCID 178525127, Verbindung

HRID 1443383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443383
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17](=O)[NH:18][CH2:19][C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:33].CC(O)=O.C1(C)C(C)=CC=CC=1>[Cl-].[Na+].O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17]1[NH:18][CH:19]=[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:33]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 7237O-XyleneHCID 517165Ammonium AcetateHCID 235707182-(2-Oxo-2-phenyl-ethylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester

Produkt 1

HCID 178525127HCID 178525127, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
165 °C

Versuchsvorschrift

2-(2-Oxo-2-phenyl-ethylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester (22.83 g, 60 mmol), NH4OAc (ammonium acetate) (63.5 g, 824 mmol), AcOH (acetic acid) (30 mL), and xylene (350 mL) were mixed at room temperature, and with stirring the reaction mixture was warmed in an oil bath at 165° C. for about 6 hours. The reaction mixture was then cooled to room temperature and poured into brine. The organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure to yield 31.24 g of off white powder. This sample was triturated in ethyl ether (100 mL), filtered, and rinsed liberally with ethyl ether to yield 15.12 g (70% over two steps) of the desired product 2-(4-phenyl-1H-imidazol-2-yl)-piperidine-1-carboxylic acid benzyl ester as a white solid. HPLC analysis showed the compound to be 100% pure at 254 nm and 98.1% pure at 214 nm.

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto yield 31.24 g of off white powder
  6. customThis sample was triturated in ethyl ether (100 mL)
  7. filtrationfiltered
  8. washrinsed liberally with ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0be0f861e169404ba1e17acc78406bd4
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659402B2

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